4,4-Dimethyl-1-nitrocyclopentene | 144605-80-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4,4-Dimethyl-1-nitrocyclopentene
• 英文别名: 4,4-dimethyl-1-nitrocyclopentene
• CAS: 144605-80-1
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: SHLULDSGKXSLKW-UHFFFAOYSA-N

物化性质

• 沸点：
  200.9±10.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4,4-二甲基环戊烯 在 sodium hydroxide 、 mercury dichloride 、 sodium nitrite 作用下， 生成 4,4-Dimethyl-1-nitrocyclopentene
  参考文献：
  名称：

  烯胺酮与1-硝基烯烃的反应。聚喹烷合成的范围和局限性

  摘要：

  The reaction of several 2-aminocyclohex-2-en-1-ones with cyclic nitroolefins has been explored as a possible synthetic approach to polyquinanes. 2-Pyrrolidino, 2-piperidino and 2-morpholinocyclohex-2-en-1-one react with 1-nitrocyclopentene to provide substituted triquinanes. Reactions involving 5,5-dimethyl-2-morpholinocyclohex-2-en-1-one were unsuccessful as were those using 4,4-dimethyl-1-nitrocyclopentene. 5-Methyl-2-morpholinocyclohex-2-en-1-one and 1-nitrocyclopentene provide the corresponding triquinane, plus a by-product in which the amino substituent has been lost. The reactions of other selected nitroolefins have been carried out, and the products are described. The results of these reactions are rationalized in terms of an inverse electron demand Diels-Alder reaction to afford an intermediate oxazine N-oxide, which then undergoes further transformations to afford the observed products.

  DOI：

  10.1016/s0040-4020(01)80490-7

文献信息

• Reactions of enaminones with 1-nitroolefins. Scope and limitations of a polyquinane synthesis
  作者：John W. Huffman、Melanie M. Cooper、Barnabe B. Miburo、William T. Pennington

  DOI：10.1016/s0040-4020(01)80490-7

  日期：1992.1

  The reaction of several 2-aminocyclohex-2-en-1-ones with cyclic nitroolefins has been explored as a possible synthetic approach to polyquinanes. 2-Pyrrolidino, 2-piperidino and 2-morpholinocyclohex-2-en-1-one react with 1-nitrocyclopentene to provide substituted triquinanes. Reactions involving 5,5-dimethyl-2-morpholinocyclohex-2-en-1-one were unsuccessful as were those using 4,4-dimethyl-1-nitrocyclopentene. 5-Methyl-2-morpholinocyclohex-2-en-1-one and 1-nitrocyclopentene provide the corresponding triquinane, plus a by-product in which the amino substituent has been lost. The reactions of other selected nitroolefins have been carried out, and the products are described. The results of these reactions are rationalized in terms of an inverse electron demand Diels-Alder reaction to afford an intermediate oxazine N-oxide, which then undergoes further transformations to afford the observed products.